I decided a little while ago to do a POD print collection of my published works so far, because I'd like to get them out there and publishers don't often take collections. The stories themselves have all already been edited by the market that published them, but there will still be things to fix, and I'll need to standardise the spelling and grammar.
The first thing I needed to do was pick the order of the stories, which isn't as simple as it sounds. It took three days when I was expecting it to take a lunch hour, two at most. Most of my published stories are flash, so there are a lot of them. Plus I've done some genre-straddling too, which runs the risk of things getting a bit disjointed. I did some Google-fu, and came up with this article, which was very helpful.
A lot of the suggestions are, of necessity, contradictory - what works for one collection won't for another, and it's a set of guidelines rather than a description of the One True Way. What I took to heart was putting the novella ("The Reflection of Memory") at the end, which I was leaning towards anyway, and starting with something upbeat.
This is when I realised I don't really do upbeat. A lot of my stories have a dark thread so I ended up going with "In Search of Camanac" as it's somewhat hopeful. It's also the first story of mine that saw print, so it seemed like a good way to start.
Another suggestion was to decide on a structure and then order the stories according to that logic. Since I had the novella at the end, and a short story at the beginning, I went with the hourglass shape: short stories, slightly shorter stories, flash, short stories (starting with the shortest) and then the novella.
The next part, picking the order of the stories within that structure, was a lot harder than it looked. It took three days. Because I've written across several genres, speculative and mainstream fiction, I needed to somehow link the stories. First I wrote a list of the titles, and any themes that applied to them, then flagged any that seemed to be natural partners, like the fairy tales, historical fantasies, and clockwork-themed. Then I wrote a list of numbers that corresponded to the number of stories I had and filled in the set points - beginning and end, and the two that sat nicely lengthwise between flash and the longer shorts.
To organise the short stories I did what can best be described as a wibbly-wobbly Venn diagram, where I wrote down the title and drew bubbles around them to link them by theme. It became really obvious then that I had a problem in the shape of "Dark Ghosts and Flamingos", which is best described as a space opera with aliens and hookers. None of my other short stories are science fictional, and I couldn't put it with the flash sci fi without violating my otherwise carefully ordered structure. Likewise, "Mr Bad Man" links nicely with "Reflection" in terms of theme, but being real-world set sticks out like a sore thumb amongst my largely secondary-world fantasy. At one point I actually considered cutting one or both of them.
Eventually I realised the problem was that I'd got fixated on having the same number of short stories at the beginning and the end of the book - but the end has the novella and so could stand to lose a story and still be balanced in terms of wordcount. I took out "A Celebration in Blue Silk", which was supposed to be my linking story between "Child of the Pact" and "Reflection" (which link without it anyway) and moved it to the beginning section. Revised, I ended up with "Dark Ghosts" sandwiched between "Blue Silk" and "A World in Clockwork" (all rebellion stories) and "Mr Bad Man" between "Clockwork" and "The Clay Men" (all stories about secrets, and the latter two set in the real world with a hint of magic).
Ordering the flash was much simpler, possibly because there are more of them to play with. As they're all of a similar length, the only structure I had was to link thematically to the ones already in place. Plus I wanted "And a Cup of Good Cheer" somewhere near the middle, since it's my one and only Christmas story to date. Along the way I made some surprising connections I hadn't even noticed. I've got a structure that I think works well, and now I'm in the process of putting the stories into the manuscript.
This is taking longer than expected too.